


Everything Will Be Alright

by wickedlittlewordsmith (hurricaneredd)



Series: I'll Be Here Waiting (I Just Need Time) [1]
Category: Critical Role (Web Series)
Genre: Brief mentions of the Traveler & the Wildmother, F/M, Fluff, Gen
Language: English
Status: Completed
Published: 2019-10-06
Updated: 2019-10-06
Packaged: 2020-11-24 07:00:33
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,528
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/20903555
Author URL: https://archiveofourown.org/users/hurricaneredd/pseuds/wickedlittlewordsmith
Summary: After everything that's happened the past few days, Caleb seeks out Jester, wanting to make sure she's okay after facing another dragon. While they spend the night in the Cinderrest Sanctum, they have a little heart-to-heart.





	Everything Will Be Alright

**Author's Note:**

> This is a part of the Widojest Art-Fic Collab event. The amazingly talented themuffinbee created the lovely art for this fic, and you should all check them out on tumblr!
> 
> The prompt for this collab was "memories"

A bead of sweat rolled down her cheek, and Jester brushed it away mindlessly as she wandered through the cavernous halls of the Cinderrest Sanctum. She was in search for an empty, hopefully discarded room—somewhere, _ anywhere _ for her to steal away to for a few minutes. Between their going up against another dragon, committing a high stakes heist in order to get Caduceus’ residuum, and the journey back from Utherdurn to Kravaraad all in the span of a few days, she was feeling a little too wound up. Not to mention the talk with Cad…

Hands tingling, chest tight, she found herself feeling too much like an exposed nerve, a jolt of energy coursing through her body as she bounced down another hall, the heels of boots clicking and echoing as she peeked into little nooks and crannies, spying potential little hideaways.

Lips curling downwards into a small pout, she’d almost given up hope of finding somewhere a little more comfortable when she spotted what looked like a room tucked away from the rest of the sanctum. Unable to help herself and thrumming with anticipation, she skipped over to the door and reached for the handle, only pausing long enough to see if anyone had followed her. Confident that she was alone, she pushed the door wide open and went inside, not bothering to close it after her. She wouldn’t be here very long, after all. Just long enough to collect herself before joining the others for the night.

*

Caleb sighed. The talk with Nott hadn’t gone exactly how he’d hoped, but while he still worried over her, he knew better than to try and push further, so he dropped the conversation, letting Nott slip out of the chamber without question.

_ One conversation down, one more to go _ he thought.

Standing up, he stretched a little, groaning as his muscles protested his sitting on the hard ground for so long. While he was certainly more than willing to help Caduceus on his mission for the Wildmother, the wizard couldn’t deny looking forward to sleeping somewhere a little bit more comfortable than either the outdoors or the Sanctum.

Double checking his components pouch and his holster for his books, Caleb headed out of the chamber in search for a certain trickster cleric of theirs.

He didn’t know where Jester had managed to sneak away to, but after searching for twenty minutes and seeing far more of Beau and Reani than he ever wanted, Caleb was about to call it when he heard a little mreow and felt Frumpkin pressing his head against his shin.

“Do you know where our favorite tiefling is, hmm?” he asked his familiar, leaning down to scratch under his chin. Frumpkin pushing his head into his hand drew a smile from the redhead, and he indulged him in some loving little scritches for a minute. “Let’s see if we can find her, ja?”

The answering trill was enough for Caleb, and he followed the cat down the winding halls of the Sanctum until he finally saw the open door hidden far away from the main living area. He was impressed Jester managed to find this place at all, but he didn’t give it any more thought as he made his way towards the room.

He stopped just before entering.

Jester sat alone in a particularly small and empty room, tucked away into a tiny alcove with her own journal open and resting in her lap. Even from this distance, he could see the signs of her concentrating hard on her drawings. She had a habit of her tongue poking out between her lips when she was really invested in getting the details just right, and as she dragged the piece of charcoal across the page he couldn’t help but watch in wonder.

Steeling himself, he made sure his presence was known as he crossed the threshold.

“Jester?”

Her head shot up in surprise, and he fought back a tiny smile at the tinkling little bells on her horns as they jingled with the sudden, sharp movement.

“Cayleb!” she said, her voice a little higher than normal. She quickly slammed the book shut and shoved it unceremoniously in the bright pink haversack of hers. “What are you doing here?”

“Ah, well—” he scratched the back of his neck nervously, fighting the urge to shift his weight from one foot to the other. “I came to see how you were feeling,” he finally answered. “You know, after we faced a dragon and everything.”

After spending so many months together, Caleb liked to think he knew most of Jester’s smiles by heart, so when she smiled just a little too wide and forced a happy, dismissive little laugh he knew that she was putting on a front, even after she tried to wave away the concern with an “I’m fine! I’m fine!”

Frowning, he stepped further into the room, closing the distance between the two of them so that he could talk a little more softly in hopes of reassuring her.

“You know it’s okay if you are not okay, ja?” he asked.

She blinked, and for a moment he thought she might continue the charade, but then he watched as her shoulders dropped, and she sighed. Without hesitation, he sat beside her, squeezing into the alcove as best he could without crowding her.

“It’s just—”

She cut herself off and curled into herself, pressing her knees against her chest and wrapping her arms around herself. Caleb waited patiently for her to say whatever it was she wanted to get off her chest, silently prodding Frumpkin to rub his face against Jester’s leg.

He watched as she idly reached out and ran her hand down the length of Frumpkin’s entire body a few times. Whatever it was she wanted to tell him, he was willing to wait for her.

“You know, it was really scary, you know?” She stole a glance out of the corner of her eyes, and he made sure he gave her an encouraging nod, urging her to continue. “I mean, it wasn’t the same as the Happy Fun Ball, obviously, but it was still really, really scary. I mean, it was an _ ancient white dragon _! Who knows what could’ve happened if we had to really fight that thing.”

As she rambled, he stayed quiet, but his mind was racing. They’d gotten lucky, it was true. By sheer dumb luck, they not only managed to get iceflex but also escaped relatively unscathed. He didn’t really believe in any one particular god, not like Jester believed in the Traveler or Caduceus believed in the Wildmother, but he wouldn’t dare think either deity wasn’t there for their respective clerics.

“And everyone was all buffed up but me, and you and Fjord and Caduceus weren’t even there for any of it!”

Her pitch had risen the more she spoke, and when the words finally spilled out, he felt a sharp pang of guilt clutch his heart and squeeze. If there was one thing he did regret, it was that he wasn’t there to have her back.

“Oh, Jester.”

If only she knew…

If only she knew how much he hated himself for hiding away in the bubble while she and Nott and Beau risked their lives for the mission. He knew logically that it was the smartest decision they could have made. Their barely escaping in time was proof of that, but he’d promised her she wouldn’t be left alone, that he’d be there for her, and he’d broken it and left her to face something she’d feared on her own.

“I was really scared, Cayleb,” she whispered, and as she met his gaze he could see her eyes shining bright with unshed tears. “What if something happened and I couldn’t save anyone in time?”

“But you know what?”

“What?”

“You and Nott managed to do what nobody else could. You managed to steal from an ancient dragon—” He pitched his voice lower, more conspiratorially as he continued, “_ And _ you left a figurine of the Traveler behind. Who can say they did that, huh?”

She sniffled and gave him a watery smile, but it was one of the most genuine smiles he’d seen from her in a while, so he took it, returning it with a crooked little grin.

Without warning, he found himself wrapped up in strong blue arms as Jester hugged him tightly, burying her face against his neck.

“Thanks, Cayleb.”

The words were muffled by his cloak, but the vibration sent a small chill down his spine. Hesitantly, he returned the hug, holding her as close as he dared before quickly pulling back, his entire face burning brightly.

Clearing his throat once more, he tried to casually lean back against the wall, which earned him a slight giggle from Jester as she happily crowded his space. She pressed up next to him, her side flush against his. If he wasn’t already aware of her presence from their close proximity before, he was certainly aware now. Hyperfocusing on the way she basically molded herself to him, he tried in vain to steady his racing pulse, inwardly cursing at the sudden hammering of his heart against his ribs when Jester casually rested her head against his shoulder.

Despite their being inside a volcano, he felt Jester shiver.

“Here,” he said, doing his best not to jostle her too much as he removed his coat. Once free of the piece, he opened it as much as it could and draped it across their laps. “No sense in catching a cold, ja?”

He was rewarded with another giggle and a flash of a grin before she gave a quick “Ja” in response.

Scheiße. What was she doing to him? He wasn’t a teenager anymore. He shouldn’t think it so endearing to hear her speak his native tongue, shouldn’t be blushing like a fool when she invades his space without a single care in the world.

“Do you think, after we save Yasha and beat Obann and the Laughing Hand, that we could visit Nicodranas for more than a day or two?” Jester asked, breaking him free from those thoughts and redirecting him.

He didn’t think it would be so easy, doing those things she’d mentioned, and he couldn’t promise her that they’d all make it out alive, but he was not about to ruin the mood by giving voice to those thoughts. Instead, he indulged her.

“I think so.” Caleb would be lying if he said he didn’t like the idea of settling down in Nicodranas. The cool ocean crashing against the shore and the warm sand beneath his feet, it sounded like the perfect place to vacation. “I would like to see more of where you are from.”

“Me too!” she said excitedly. “It’s so beautiful there, and Mama is there, and Bluud!”

She moved quickly, sitting up and twisting to face him better, and if he felt a distinct sense of loss at not having her against him, he quickly shoved it down the moment she took his hands in hers.

“And maybe, maybe, we can go visit your home, too! You know, after we get rid of Dickithon.”

She’d said the name with such utter disgust, scrunching her nose and shaking her head as if even just uttering the crude nickname left a foul taste in her mouth. He fought the faint smile, but he must not have succeeded by the beaming, impish grin Jester shot him.

“Maybe, Schatz,” he conceded. “But only after you have a nice, long visit with your mother.”

Jester nodded enthusiastically at that, and the soft tinkling sound drew a smile to the wizard’s lips. Try as he might, there was no fighting Jester’s presence. It was so heady that he found himself opening up a little.

“You know,” he whispered conspiratorially, leaning forward and shooting her a secretive grin. “I actually had a really interesting talk with your mother that night we teleported there.”

As expected, she perked up and leaned forward. They were close enough now that he could feel the warmth of her breath against his face, and he suppressed the shudder that wanted to course through him.

“What did you talk about?”

“Ah, that”—he leaned back against the wall of the alcove and shrugged noncommittally—“you’ll have to ask your mother.”

It was a good thing she wasn’t pressed against him the way she’d been earlier, or she’d have felt the way his heart thumped at the idea of Jester finding out what he’d talked to her mother about.

She pouted, though, and he bit the inside of his cheek to keep from laughing. She was too much, and the longer he spent with her the more she wormed her way into his heart.

With an exaggerated huff, she threw herself back against his side, going even further than before by casually throwing her legs over his and tucking in unbelievably close.

“What was your home village like?” she asked innocently, and if he didn’t know her better, he’d suspect her of fishing for information about his past. But he did know her and knew that there was no ill-intention behind the question, just genuine curiosity.

Perhaps it was because they’d both been a little too raw and vulnerable with each other not too long ago, or maybe it was because her presence was simply that intoxicating, but whatever the reason, he found himself opening up.

“Blumenthal is a—it is small. It’s a small village,” he started, stumbling over words here and there as his mind raced, “just outside of Rexxentrum. It—we were not a particularly well-off village. There were a lot of farmers and soldiers in the lower ranks.”

As he spoke about his home, his mind drifted back to the village. He remembered the fields they would play in, remembered the way everything turned golden and so beautiful in the fall, only to be blanketed in snow during the dead of winter. He remembered the ruckus he and the other kids in the village would wreak at the first signs of spring, all of them exhausting the pent-up energy from the winter. He remembered the way his mother would smile at him whenever things were particularly hard and how she’d reassure him that everything would be alright.

Memories flooded his mind, some more painful than others, but as he spoke he found it easier and easier to open up to Jester until eventually he fell silent.

“It sounds wonderful.”

She’d spoken so softly that he almost missed it, and suddenly he became aware of his surroundings. At some point, Jester had laid her head on his shoulder, carefully positioned so that her horns didn’t jab him, and his coat was once more covering their laps, this time with the added presence of Frumpkin lying curled up on them. He thought that he’d be uncomfortable with her being so close, especially after opening up so much, but instead he found himself calm. Relaxed, even. Far more relaxed than he’d been in a long time. And that was something he’d worry about later. Right now, he would simply seek comfort in her presence.

“It was.”

Silence fell, and he was keenly aware of just how late it was and how long the two of them had been talking. What had meant to be nothing more than him checking in on his dear friend had somehow grew into something more, and as Jester’s tail lazily flicked contentedly against the floor, he wondered how long they could get away with their disappearing from the rest of the group.

“We should come up with cons one of these days.” Her words were slightly mumbled, and Caleb smiled faintly, wondering how long it would be before she drifted off to sleep. “You know, like you and Nott have? Only, they could be for the two of us. And maybe we can even come up with some for the Chaos Crew.”

He breathed a laugh into her hair and nodded.

“Ja, okay,” he agreed. “We can do that. But later.”

She hummed happily and nuzzled against his shoulder, moving just enough for her to get comfortable again.

He leaned down, resting his cheek against the top of her head and let silence fall between them once more. His mind drifted off as time passed, thoughts of one potential future dancing in his mind’s eye, and he almost believed Jester had fallen asleep when she spoke once more.

“Cayleb?”

Her voice drew him out of his reverie, and the wizard awkwardly cleared his throat as he pushed those thoughts away.

“Ja?”

“Tell me a story?”

The request was so simple, yet it still caught him off guard. Shifting slightly, he hoped she wouldn’t look up to see the way his cheeks burned at being caught off guard.

“Oh, uh—what, uh, what kind of story would you like to hear?”

She hummed softly, eyes slowly drifting close as she pressed closer. “Something happy.”

Maybe it was because they’d been talking about his childhood, or maybe it was because he’d had so few happy stories, but Caleb instantly drifted back to one of his most cherished memories, remembering one of his favorite stories his mother would tell him before she’d kiss him goodnight. He still remembered the way she’d weave magic with her words. Could still recall how she captivated him with the story of a poor girl going from servant to princess.

“Have you ever heard of the story of Aschenputtel?” he asked.

He didn’t see so much as he felt her scrunch her nose in thought. Being this close to her, he was hyper aware of every shift of movement she made, could feel every breath she drew in before exhaling. But he knew all too well what she looked like when she did that. If he were an artist, he could paint every detail, from the way she would purse her lips, the bottom one jutting out a little further, to the way her brows furrowed slightly. He would know exactly how the freckles that dusted the bridge of her nose would be lost in thatlittle crinkle.

“Nein,” she answered, her lilting Nicodrani accent somehow making the Zemnian sound more musical than it had the right to. She shifted again, this time tilting her head up just enough to look up at him, and despite the warmth of his cheeks he couldn’t help but meet her gaze, a crooked little smile tugging at the corner of his lips. “Is it a happy story? Like, really happy?”

He nodded, and the small smile he was rewarded with made his heart stutter and his cheeks burn a little hotter. Clearing his throat, he willed himself to relax and was rewarded with more snuggling from both Jester and Frumpkin, the latter purring softly as he stretched and rested his head in Jester’s lap.

“There was once a rich man whose wife lay sick,” he started, closing his eyes as he recalled the story, “and when she felt her end drawing near she—”

He felt a sudden jab against his ribs and stopped instantly, peeking down to catch the slight frown dancing on her lips. A momentary lapse in judgment had him imagine what it’d be like to lean down and press his lips against hers, stealing a kiss (or two or three), but before he could act on impulse he shoved the idea away, coming to his senses just long enough to catch what she was saying.

“Caaaayleb,” she drawled out with a huff, “that’s _ not _ happy.”

He chuckled and shook his head. Always so impatient, his little blue tiefling was. And while he would normally indulge her, he knew that a little bit of sadness was worth enduring for the happy ending. Instead, he leaned further back into the alcove, being extremely careful not to jostle either of the two precious beings currently curled against him.

“Do not worry, Schatz. It will all be worth it.”

Jester’s only response was an exaggerated roll of her eyes and a noncommittal hum, which he took as the okay to continue telling the story.

Somewhere around the second night of the dance Caleb noticed Jester had fallen asleep, and while he felt sleep calling to him he watched the steady rise and fall of her chest, drinking in every little detail. From the way her hair—longer now than it’d ever been—fell into her face, to the slight jingling the bell on her horn made every time she shifted, to the way she’d clutch his coat in her sleep, he took it all in. This was a memory he never wanted to forget.

*

It wasn’t until the early hours of the morning that anyone from the Mighty Nein went looking for the two of them, and when Nott peeked in and saw Caleb and Jester curled against one another with Frumpkin using both of them as his personal mattress, she quietly closed the door and silently crept back to where the others were sleeping.

(The amazing art from @TheMuffinBee on [Tumblr](https://themuffinbee.tumblr.com/post/188176374810/this-is-my-half-of-the-widejest-collaboration-with))

**Author's Note:**

> AHHH!!! I can't believe I finished this!
> 
> For those of you who were curious or wondering about the story Caleb tells Jester, "Aschenputtel" is the Grimm Brothers' original title to Cinderella. I thought it'd be a nice little tidbit to include since Zemnian is basically German and all that jazz. (Plus it lets me indulge in my fairy tales studies!)
> 
> This...has somehow turned out to be the first of a series of one shots I have planned. Some of them have been hinted at in this story, and some are way further down the line, so those are all things to look forward to!
> 
> Please, any and all feedback is appreciated! Let me know what worked for you and what didn't work, or you can even let me know what you wanna see happen.
> 
> Anyway, see you all next time!
> 
> P.S. – Shout out to the awesome peeps in the Widojest Server on Discord for answering my dumb, panicky question earlier! You’re all super amazing!


End file.
